


Bully

by transcherrylove



Category: Original Work
Genre: Anal, Anal Fingering, Anal Fisting, Anal Gaping, Anal Play, Anal Sex, Blow Jobs, Bullying, Cumdump, Deepthroating, Double Penetration in One Hole, Double Penetration in Two Holes, Fear, Glory Hole, Inanimate Objects, Object Insertion, Object Penetration, Painful Sex, Power Dynamics, Public Sex, Rape, Rape/Non-con Elements, Trans Character, Trans Male Character, Vaginal Sex, Violence, Watersports, comedump
Language: English
Status: Completed
Published: 2020-04-14
Updated: 2020-04-14
Packaged: 2021-03-02 01:26:57
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 4,315
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23646904
Author URL: https://archiveofourown.org/users/transcherrylove/pseuds/transcherrylove
Summary: Ben’s still new at school, nobody knows he’s trans. Well, until his bully low-key hears about it.
Comments: 5
Kudos: 277





	Bully

**Author's Note:**

> I do not promote or condone this behaviour beyond fiction.  
> Word Count: 4314
> 
> You can find me on Tumblr, Twitter, IG, and Onlyfans under the same username - transcherrylove

Ben was reasonably new at school. He’d been there more than a semester but nobody new had come, so he was still the new boy. He wasn’t the luckiest guy in the world, he’d decided that when he realised that his vagina didn’t make him a girl and got beaten and thrown out of his house for it. He was an orphan now, and yeah he got bullied at the home but the place was a sanctuary in comparison to school.

See, school was the only place he saw Kyle, and Kyle wasn’t the kindest of people. Not that the rest of the school thought this - even the teachers loved him. He was a prize to the school, a star athlete and the boy who helped even the nerds out. He was well known for being sweet hearted and unprejudiced. Which is why Ben was unable to say anything.

Only Ben had seen Kyle’s dark side. He wasn’t sure why he was picked out of the crowd, but any chance Kyle got alone with him, he’d always kick him in the ribs or lock him in a locker or an empty classroom on the top floor. He’d locked him in the sports shed overnight once, and he really loved shoving his homework and notebooks in puddles.

To be honest, Ben didn’t think Kyle could get any worse. He was a jerk, but he’d seen plenty of jerks and Kyle was the worst so far, so imagining even worse scenarios was quite hard. But that was very fast to change.

He wasn’t sure what had pushed Kyle to extremes, but it was the first class turnaround of the day and Kyle was already shoving him into an empty classroom. Ben had given up at the first sight of him, and he fell back onto his ass with a groan, accepting his fate of missing the next class or two. He was expecting to spend that time in silence as usual, but Kyle had locked himself in the classroom with him, and Ben was more confused than he had been in maths class.

“I have a request,” said Kyle, grabbing Ben’s shirt and pulling him up to stand. “Strip.”

Ben’s eyes widened. He knew that wasn’t a request, but it was so strange and uncharacteristic that he stood dumbly for a moment. Kyle, however, was fast to lose his patience. He grabbed Ben by the neck and pushed him against the wall and Ben cried in pain as his back hit the light switch, turning the classroom lights off. The light from the windows lit up the room now, but the dullness of the room made Ben’s heart pick up even more.

“When I tell you to do something, fucking do it,” Kyle said deeply, and Ben really wanted to cry. “Take your clothes off or I’ll cut them off and you can walk home naked.”

Ben pulled at his tie with shaky hands, and Kyle leaned against one of the front desks curiously. Ben didn’t have a penis, he wasn’t sure how much Kyle wanted him to take off, so he took his cardigan and tie off and stopped there.

“I’ll level with you,” Kyle said calmly, looking at his fingernails. “Jayson mentioned that he knew a guy who said you had a pussy. Not sure why it took so long for him to tell me this but now I’m curious. I want to see a boy pussy. So you have the choice now to let me see and I can be nice, or you can try and stop me and you know how well that will end.”

“Kyle...” Ben mumbled. “It’s true...you don’t need proof I’ll just tell you it’s true...”

“I want to see,” Kyle said, sighing in irritation. He was getting impatient and Ben nodded quickly before Kyle could become irrational. He hesitated only a moment before unbuttoning his shirt. He couldn’t afford a binder, but he was blessed with a very small frame and thus a small chest, small enough that he could get away with a sports bra and be flat enough to pass without question.

He swallowed as he unbuttoned his pants, and along with his shoes he left them on the floor beside him. He stood with his sports bra and boxers on, hoping that it was proof enough, but Kyle stood up and front of Ben, who stiffened starts the proximity.

Kyle pulled the sports bra up roughly, and Ben managed to lift his arms to pull it off the rest of the way, his arms shaking in fear as Kyle’s hands fisted his boxers on either side.

“Wait! Ky-“

Kyle pulled the boxers down, and Ben sobbed in embarrassment as he felt them pool around his ankles. His eyes were squeezed shut as Kyle’s eyes zoned in on his trimmed pussy, hardly glancing at the small breasts.

“Holy shit,” he grumbled. He pressed a hand against Ben’s chest grabbing a breast as he pinned him against the wall, while the other he used to pull Ben’s lower lips apart to see his large clit. “Dude it really is a boy pussy. You ever been fucked before?”

Ben nodded reluctantly with tears rolling down his face, and Kyle hummed, then pinched his nipple, eliciting a pained yelp from the boy.

“Bend over the desk,” said Kyle, and Ben shook his head quickly, about to protest aloud, but Kyle was faster and grabbed his hair, pushing him to the side and forcing him to bend over the desk, his hips hitting the edge and his knees bent a little. “Good boy. If you do what I say I’ll make it a bit easier on you. But kid, if you don’t listen I’ll make it fuckin hurt. Got it?”

Ben could only nod as he felt hands on his bare ass. They retreated for a moment and he saw his bag being shoved on the desk next to them. Kyle rummaged through Ben’s bag and grabbed his pencil case, before disappearing behind him again.

He heard the pens and pencils moving around, and they stopped for a moment only for Ben to feel fingers pulling his lips apart. Ben heard Kyle spit, and then gasped as he felt a wet glob of saliva land right against the hole of his pussy.

“Better not make noise. I locked the door but teachers have the keys.”

Ben’s eyes widened is when he felt a pencil being pushed into his hole. Thankfully Kyle was slow, and definitely used the blunt end, but he didn’t pull it out, he felt another pencil being pushed in next to the first one, and Ben hung his head as he silently screamed for help in his mind.

Kyle pushes another pencil in, deciding that he wanted to put the small collection of colouring pencils in his new toy. There was about ten of them, and they slipped in fairly easily. Kyle was having fun watching the boy’s pussy stretch around the pencils, but he hadn’t made any signs of pain. Kyle grabbed a thick sharpie and used his torso to keep the pencils inside his toy, before spitting directly onto Ben’s virgin asshole.

This was what made Ben look up.

“No, Kyle! Not there please!! Wait you ca-!”

Ben squeaked a little as Kyle pushed the sharpie into his ass, enjoying the way the muscle opened up around it so well. He grabbed a highlighter, both it and the sharpie about the size of two pencils, and pushed it in next to the sharpie. Ben sobbed in horror and discomfort. It wasn’t painful yet, but the feeling of having something in his ass made his feel sick and was started squirming and trying to push them out, only to allow them easier access to settle deeper.

Ben felt another being pressed against his ass, and this time it was hurting. Kyle has been spitting on them to get them in easier, so it wasn’t dry, but it was stretching him more than it naturally should have been stretched, and Ben was biting on his fist to stop his cries.

Another marker was pressing against this hole and this time Ben reached back in a panic, only for his hand to be slapped away. He felt a hard slap on his ass cheek that echoed through the room, and Ben yelped in pain as it made him jerk back, pushing the pencils and markers deeper into him as he pressed them against Kyle’s torso. Ben suddenly tried to jerk forward in shock, but Ben pressed against his lower back and shoved the fourth marker into his ass, and Ben squealed quietly in pain as it sank into his rectum.

“Ow, ow please Kyle, please stop it’s enough!”

He didn’t realise his pleas we’re turning his molester on, but Kyle was quick to decide on a change of plan. He pulled the markers from Ben quickly, who yelped in pain as he did so, only to pull the pencils all out in one go. Kyle shoved them all in Ben’s bag along with the open pencil case before grabbing his lunch box from inside, which consisted of a tangerine, an apple, and a pop tart. He left the pop tart and tangerine, grabbed the banana, then lined it up with Ben’s pussy.

“Kyle it’s too dry!”

Kyle pauses a moment, and to Ben’s surprised he agreed.

“True,” he grumbled, and Ben glances back when he heard the banana being opened. He turned back around in horror, and he felt the end of the banana lined up with his pussy. “This should be better, since you’re being a good boy.”

Ben pushed his palm against his mouth as Kyle pushed the peeled banana into his stretched pussy. It felt strange and still dry, but it didn’t hurt like the skin could have, and when Kyle pulled it out it was wetter than before.

“You’re so soaked you’re lubing the banana up yourself,” Kyle scoffed. “And you act like you don’t want this...”

Kyle started thrusting the banana into his toy’s pussy, watching the outer layers become mushy and collect around his stretched opening. Ben didn’t want to admit that being fucked by food felt good, and it didn’t hurt. Still, he wanted it to be over. He was humiliated and he wanted to go home. But Kyle kept pushing the banana into his pussy, and eventually Kyle pulled it out and stayed silent for a moment.

Kyle had broken off some of the banana and chewed it up. He knelt down and pulled his toys lips apart, pushed his own lips to Ben’s entrance, then slowly spat the mushy banana into his toy. Ben was holding the desk for dear life, realising that Kyle was so much more fucked up than he’d ever witnessed before. He could feel the banana filling him up, and Kyle would pull away to chew some more, only to spit it into him. And Ben was a little more relaxed after a minute of this, since there was no pain, but Kyle hummed and used his fingers to push it further into Ben before stepping back.

“Keep that in, slut, and put your pants and shirt back on,” he said, shoving the boxers and bra into the bag and throwing Ben’s bag into the corner of the classroom. Ben hurried this time, he tried hard to keep the banana inside him as he dressed himself fearfully, but he was relieved to put his clothes on again.

Kyle grabbed his elbow and pulled him out the classroom and into the empty hallway, and Ben followed obediently. Kyle pushed him into the janitors closet, and Ben thought he’d finally leave him alone here, but his heart picked up again when Kyle piled in with him.

“Strip.”

Ben’s tears flowed again, and he silently followed his order whilst doing his best to keep the mushy banana inside his pussy. In the closet was a bunch of boxes in the back, a stool, a ladder, a sink, and a lot of cleaning supplies.

Kyle’s imagination went wild, but eventually pushed Ben down in the same bent over position over the boxes, then grabbed a towel and shoved it over his head so Ben couldn’t see.

Kyle grabbed a scrubbing brush from the bucket that had a rounded handle, ran it under some soap and water, before heading to the helpless boy on the boxes. He lined the handle up with the banana filled pussy and pushed it in, watching in fascination as the banana seeped out around it as he pushed it deeper. He didn’t hear Ben’s cries very much, he was enjoying thrusting the handle of the brush into his toy, the banana squelching out with each push.

But Kyle got bored quickly, so he pulled it out and lined it with Ben’s asshole, and he started pushing in slowly. Ben squirmed this time, but it didn’t stretch him any wider than the markers had. He pushed the handle in as deep as it would go, before turning to find something else he could play with. There was a bottle of insect spray on the top shelf, probably the size of a tennis ball. It wouldn’t fit inside...yet.

Kyle washes the bottle and set it beside Ben, then pulled the brush from his ass. Kyle used hand soap on his hand and pushed three of his fingers into Ben, who stiffened at the realisation that there were actual human fingers in his rather than cold objects. Kyle pushed a fourth finger in, and he took his time as he pushed his fingers in deep. He managed to get half his hand in Ben’s asshole, until only his thumb and the bottom of his hand was out. He pulled his hand out and shaped it like a cone, pushing back in slowly.

Ben was sobbing, and although it wasn’t loud it wasn’t exactly quiet. Kyle wasn’t worried, people locked themselves in here to cry all the time, nobody would bother them.

He kept thrusting his hand against the tightly stretched hole, spinning his wrist as he went, and he slowed almost to a stop as he pushed his hand against the hole. He was almost there, it was so tight, and Ben lost all logical thought as he tried to push the fingers out like a shit, only this allowed the hand to pop past his ring of muscle and Ben slapped a hand over his mouth as he screamed in pain.

“K-Kyle,” he sobbed, feeling his hand squirming inside his asshole. “Please, please take it out I’ll do whatever you want just stop. I’ll never say anything I swear just let me go home...”

Kyle ignored him, pulling his fist out, watching as Ben’s hole followed. Ben sobbed as he pulled his hand out, only to push it in again, and as he sank his hand in, he watched as Ben’s hole swallowed him up, tightening around his wrist. The boy’s body twitched and pulled against his hand. He never knew it was so warm inside an asshole.

Kyle pushed in deeper, feeling his sphincter slowly straighten around his hand, and Ben gasped loudly as if something was squeezing his lungs. Kyle pulled back, then thrust in again, slowly working his hand deeper and deeper until Ben’s hole was wrapped halfway up his forearm.

Slowly, he pulled his hand out, and Ben’s hole gaped open as Kyle smirked at his progress. He pulled his pants down and jerked himself off as he pressed the end of the insect spray can against Ben’s hole. It opened up easily around the metal can, and Ben jerked at the coldness of it as it sunk into him slowly. Kyle began thrusting it in slowly, in and out as he jerked himself off at the same time, and it with all that had happened so far it didn’t take him long to reach climax. He pulled the cab out, pointed his cock at the gaping hole, and shot his load in Ben’s raw and wide asshole.

Ben felt it shoot inside him. He didn’t need to guess what it was considering it was accompanied by a grunt of satisfaction. He just continued crying under the towel.

Kyle decided he was done for the day. He didn’t want to overdo it on the first day, Ben was his toy now and would be able to take him whenever he likes, so he slapped Ben’s ass and walked to the door.

“I’m leaving now. Janitor will probably come soon so you better get dressed and leave.”

With that, Kyle left and shut the door behind him, and Ben didn’t know why he didn’t feel relieved. He needed to go back to the orphanage. He was safer there.

Ben had been off school a week because he hadn’t been able to walk properly, and his asshole still gaping when he looked in the mirror. He was scared it would stay like that forever. He was glad there had only been pencils and banana in his pussy, he wasn’t sure he’d have been able to handle any more in there.

He probably should have told someone he was being bullied, they might have helped him change schools again, but instead he again found himself in Kyle’s grasp, who happened to be angry about his disappearance.

Kyle had beaten him in the locker rooms early in the morning, and then took him to the boy’s bathroom that was located beside the stairwell to the basement. As far as Ben knew, nobody used these bathrooms since they were too far away from the classrooms, but he allowed Kyle to drag him limping to those bathrooms since he hadn’t much of a choice.

Kyle pushed him into the floor, and Ben landed on his back with a painful thud. The bully straddled Ben’s shoulders and unzipped his pants.

“If you wanna run so bad I’ll give you a reason to run,” he threatened, pulling his cock out and pushing it against Ben’s lips. Ben knew too well what would happen if he let his teeth come in contact with Kyle’s cock, so he opened his mouth wide and Kyle pushed his cock inside angrily, too deep too soon, and Ben gagged loudly and flailed his limbs as his breath was cut off. “Shut the fuck up, whore. You’re gonna be taking so many dicks at recess this is nothing.”

Ben didn’t even process the words, he was focused on the cock that was sliding in and out of his throat roughly, barely letting him breathe as Kyle fucked into his mouth. His cock was wet and salty, it was slim, so it didn’t hurt his throat too bad, but it was long, and it slid so far down his throat he didn’t realise it was possible until then.

Kyle fucked Ben’s throat raw, and suddenly he pulled about and squirted his cum over Ben’s left eye and cheek, causing the boy to blink rapidly with a breathy whimper.

“Alright,” Kyle breathed, sounding calmer that before. He grabbed Ben’s upper arms and pulled his almost limp body up and over to the middle of three stalls. Ben hadn’t noticed the set up considering he was half blind with cum. Ben quickly realised his clothes had been stripped from his body, much to his fear. He didn’t want to have a can in is ass again.

The next thing was a bit weirder though. He didn’t think this kind of thing existed, but Kyle pushed him against the wall of the stall and Ben gasped as his ass and upper thighs slid through a well designed hole. There were straps bolted into the wall that Kyle tied around his thighs and hips, and Ben wanted to say ask him to stop, but all that came out was air.

Kyle bent him over, and it was almost a perfect fit as his mouth lined up with the hole in the other wall. Another strap went around the top of his head and around his chin to keep him in place, and Kyle sighed and sat on the toilet lid. Ben sniffed and cried, but was completely silent even when the bell for recess rang.

The door to the bathroom opened, and Ben started panicking and tried to move. He knew what was about to happen when he heard laughter and zips being pulled down, but the straps kept him well in place, and he immediately felt a cock push into his mouth. He squeezed his eyes shut as the stranger assaulted his mouth, and he felt another cock at his pussy. Whoever it was pushed in with a moan, and Ben cried as it filled him up, pressed so deeply he was sure it was in his stomach.

Both cocks fucked him until they came, the one in his pussy climaxing first, and it was quickly replaced with another, a bit thicker, and Ben would have grunted at the firth if his voice box was still working.

His mouth was empty for a moment, until he heard whispering, and a cock entered his mouth, he gagged as it pushed down his throat, only for it to retreat. Strangely enough, another cock pushed past his lips, and he had two cocks in his mouth, each pumping in one at a time, not getting deep but sharing his mouth while his pussy was fucked messily in the other stall.

He felt cum release in his pussy again, and the next person who came slapped his stretched asshole and made him jerk. They pushed their wet tip against his ass and slid in easily with a moan, and he cried as the two cocks in his mouth squirted down his throat.

The person who was fucking his ass pressed a finger next to his cock, and another, until they had four fingers around their own cock, all inside his rectum.

“Fuck,” they moaned, wrapping their fingers around their cock as if they were jerking it instead of fucking him. “Gotta try this mate...”

He pulled out and lined his top with Ben’s pussy, then squirted his cum inside, then left. The next one had taken the formers advice, and decided to take his ass while someone else took his throat again. The person behind him pressed their fingers in his ass, and slowly they pressed their cone shaped hand against his hole. It only resisted a little, before it popped in and Ben violently tried to get away this time, but the straps were too strong and Kyle just laughed as he watched his toy struggle.

The hand in his ass came back out, but left four fingers in, and Ben realised that another finger had been added and it wasn’t from the same hand. They started filling his ass up with more fingers from their second hand, and stretched him out by pushing one fist in and adding fingers at the widest part.

Ben was trying to scream, but after Kyle had forced his cock down his throat he couldn’t find his voice. The person behind him pulled everything out, then put two coned hands together and started pushing in. Kyle watched curiously as Ben’s entire body shook in fear and pain as two fists forced themselves to slowly squeeze past his ring of muscle, and Ben jerked with a gag as they popped inside.

The hand stayed still for a moment, before one slid deeper into his intestines, until his rim was stretched around one wrist and one forearm. They pulled their arm back to their hands again, then pressed the other hand deep, this time pushing in until Ben’s ass was throbbing just under his elbow. Ben was sure he’d never be able to use his ass properly ever again after this. It would never close properly again. Kyle was impressed, however, as he watched Ben’s stomach bulge with each thrust of the stranger’s hands.

The person behind him kept alternating their arms until they grew bored, pulled their arms out and left one hand inside him. They inserted their penis and wrapped their hand around themselves inside of Ben, then jerked themselves off from inside Ben until they came. They left, and someone else fucked his pussy, and another, and someone else used his ass again although Ben wasn’t sure how they enjoyed it when he could barely feel them anymore.

Another person came in, his mouth still being fucked, but the person behind him didn’t fuck him, they pressed a flaccid cock against his wide asshole and Ben was confused for a moment, until he realised his insides were warming up, and he started breathing heavily in a disgusted panic as the person pissed inside his ass, filling his intestines with their piss and mixing it with the leftover cum. It seemed to be the end of the fucking, because another person did the same thing, inserting their penis into his ass and pissing inside of him with a moan of satisfaction.

Finally, the voices left, and Kyle and Ben were left alone once again. Kyle unstrapped the head straps and Ben fell forward, bending over with no strength left in his body, and his head spun with disgust as he felt the urine pour deeper into his body. He barely caught himself from hitting his face in the ground as Kyle unstrapped him from the other wall, and he was left with his ass in the air as Kyle leaned over him, pulling his cock out and pressing against his ass. Ben couldn’t move or do anything as Kyle pissed into his asshole, adding to the piss already inside him, and Kyle cleared his throat as he left the stall.

“See you in another week I guess.”


End file.
